Hydrochloric Acid → N-nitroso-N-(5-methoxycarbonylpentyl)-aniline

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Reaction Steps

A solution of 1.4 g of sodium nitrite in 5 ml of water is added dropwise at 0°-10° to a mixture of 4.42 g of N-(5-methoxycarbonylpentyl)-aniline, 2.9 ml of concentrated hydrochloric acid, and ice as needed to maintain the desired temperature. The mixture is then allowed to stir at ambient temperature for 1 hour and is then extracted with ether. The extract is washed with water, dried over magnesium sulfate, and evaporated in vacuo to give N-nitroso-N-(5-methoxycarbonylpentyl)-aniline as an oil.

Provenance & Evidence